Carbon tetrabromide → 4-[(3-Bromopropyl)thio]-2,6-bis(1,1-dimethylethyl)phenol

HRID 1682542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1682542
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]([C:24]1[CH:29]=[C:28]([S:30][CH2:31][CH2:32][CH2:33]O)[CH:27]=[C:26]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:25]=1[OH:39])([CH3:23])[CH3:22].C(Br)(Br)(Br)[Br:41]>CCOCC>[Br:41][CH2:33][CH2:32][CH2:31][S:30][C:28]1[CH:29]=[C:24]([C:21]([CH3:23])([CH3:22])[CH3:20])[C:25]([OH:39])=[C:26]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH:27]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 214746842,6-Bis(1,1-dimethylethyl)-4-[(3-hydroxypropyl)thio]phenol

Produkt 1

HCID 190446984-[(3-Bromopropyl)thio]-2,6-bis(1,1-dimethylethyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Triphenylphosphine (17.54 g, 66.89 mmol) was added to a stirred solution of 2 (9.9 g, 33.44 mmol) and carbon tetrabromide (22.18 g, 66.89 mmol) in dry ether. After stirring at room temperature for 18 hours, the reaction mixture was concentrated and the crude product was chromatographed (silica gel; hexane/ethyl acetate 98/2) to give 3 in quantitative yield. The structural assignment was supported by the 1H-NMR spectra in CDCl3.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. customthe crude product was chromatographed (silica gel; hexane/ethyl acetate 98/2)
  3. customto give 3 in quantitative yield

Quellen und Nachweise

ORD-Eintrag
ord-b196dc17a74d4b98bb0678282b7b4b9e
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05635514

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